Jordan Klepper and Steve Waltien On Comedy in the Trump Era

When Jordan Klepper and Steve Waltien were aspiring young comedians in the early-2000s Chicago improv scene, they scored a string of gigs that uniquely prepared them for their later careers.

The two met as cast members on “World News Tonight,” a weekly political satire show at ImprovOlympic, now the iO Theater. Their off-the-cuff riffs on the news led to joining the fake late-night iO talk show “The Late Night Late Show” as rotating hosts. Later, with “Friday Night Tailgate” for the Big Ten Network, they traveled to Big Ten schools interviewing — and poking fun at — college sports fans.

“Looking back, it was a good training ground for our future endeavors,” Klepper said in a recent interview with Seven Days.

Klepper, 47, is best known as a correspondent and host of “The Daily Show” on Comedy Central. In that gig, he’s spent a decade traveling to President Donald Trump’s rallies interviewing — and poking fun at — Trump’s fans. Applying improv comedy principles to the thankless lot of the roving TV news reporter, Klepper exposes the absurdities and contradictions of the MAGA movement in ways that conventional journalists can’t — often by simply letting its faithful speak for themselves.

Steve Waltien Credit: Courtesy of Scott Kowalchyk

Waltien, 48, is a Shelburne native and Middlebury College grad. (Full disclosure: He and this reporter were high school classmates and remain friends.) The Second City alum worked on “The Opposition With Jordan Klepper” and was a writer on an HBO animated series with “The Daily Show” host Jon Stewart that never aired.

He was a writer on “The Late Show With Stephen Colbert” until earlier this year. Last summer, CBS announced it was canceling the show, citing financial challenges. But the move also came as the network’s parent company, Paramount, sought approval from the Trump administration for a merger with Warner Bros. Colbert, who rose to fame as a caricature of a right-wing talk show host on “The Colbert Report,” has been an outspoken Trump critic, which led to suspicion that political motivations drove Paramount to ax what was then the No. 1-rated late-night show on TV.

This Friday, July 31, Klepper brings his solo show to the Flynn Main Stage in Burlington as part of a short Northeast run, with Waltien as his opening act. Seven Days spoke with the comedians in a video call about MAGA rallies, accidentally covering the January 6 insurrection and the state of late-night TV under Trump.

Jordan, what can folks familiar with your “Daily Show” work expect to see at the show?

JORDAN KLEPPER: I’ve spent a while traveling the country, talking to a bunch of different people. And I get a lot of similar questions about America in general, about the folks that I talk to, what I gleaned from the interactions. And I wanted to put it all into a larger story and show. So I show clips; I have slides. It’s sort of a big storytelling show, and I wanted to bring it up to Burlington, bring it up north.

Steve, you and I were talking about this yesterday, but I’ve noticed as I started going on the road that people are really yearning for community, to be in a space to laugh together, to commune together. And so in figuring this show out, I wanted to make it as celebratory and fun as possible.

On this leg of the tour, you know, I asked a few people to open. They said no. And then I was like, Maybe Steve will say yes. He’s from there, so it would make sense.

So we’re not performing together, but Steve’s gonna open the show and do a great Steve Waltien piece, and we get to give each other shit in the car as we drive between these cities, just like old times.

So, Steve, what are you doing for the show?

JK: Yes, Steve. What the fuck are you doing?

STEVE WALTIEN: I … don’t know yet. [Laughing.]

I’ve opened for Jordan a couple different times, and it’s a really special show. So my job is just to warm up the crowd, get people excited. I’ll do some standup-y stuff, maybe a light character thing. I haven’t fully decided yet. Hopefully, on this stop of the tour, it’ll have some local flavor and kind of set the tone, welcome everybody in and kick the night off.

JK: Do you think they’ll like you more than me?

SW: No. I think we were talking last night about the weirdness of the local show. It’s just, like, performing for a lot of your mom’s friends and meeting those expectations.

I gotta say, talking about weird life goals and dreams, I saw a lot of shows at the Flynn Theater growing up. I’ve been lucky to perform in a lot of big, interesting places, but I don’t think I’ve ever performed on the Main Stage at the Flynn. Jordan, I know you’ve had these moments in your hometown, too — of like, that’s the first big theater that you went to, and you can still see it through your childhood eyes. And it’s like, Oh, my god, I can’t believe I’m playing the Flynn. It will always probably seem bigger to me because I was a little kid seeing The Nutcracker there or something.

JK: There’ll be a lot of Tchaikovsky in this show, as well.

SW: Yeah, I’ll probably do a Nutcracker tribute.

Jordan, you’ve probably spent more time in the MAGAsphere than most actual journalists. How have you seen it evolve over the last decade?

JK: “Evolution” wouldn’t be a word that I’d use, or one that is, I think, even legal to say at a MAGA rally. I believe that word has been wiped out.

Touché.

JK: It’s hard to glean knowledge as to what direction the movement is going from some of these events. And I’ve seen it wane.

In the last year, Donald Trump has been doing far fewer events. One, he’s not campaigning. But also it doesn’t seem as if he’s seeking out these types of mass experiences like he did, which is perhaps telling in itself.

I went to the UFC event on the White House lawn a few weeks ago — and that’s a strange sentence to utter. My expectation was that I was going to a MAGA event, but the reality was I was going to a UFC event that had some MAGA people there. That was a surprise to me, that the real draw to that event was the sports spectacle happening on the White House lawn.

So I think the MAGA movement who loved Donald Trump, who have made Donald Trump part of their identity for the last 10 years, those faithful show up and are excited to be there when the parade comes to town. It feels like we’re past the time where the onlookers who are curious about getting on board show up to see what is being said. We already know what the narrative is. We already know what that guy says, and we already know what the show is.

And from my perspective, the show’s getting a little tired. Fewer and fewer people are showing up; it’s not going as well as the show was before. It’s rambling in ways that it never rambled before. And it’s much harder to bitch about the people who can’t make change when you are the most powerful person on the planet. So I think that message isn’t resonating like it used to.

What that means, where that’s going — it’s hard to tell. I’m sure I will check back in closer to the midterms and see where they’re at.

When you first started doing this, you didn’t have the profile you have now. Has your fame changed the way you approach the segments? At least some people at those rallies must know who you are.

JK: We are in our own bubbles still, so I don’t think there’s a ton of giant “Daily Show” fans at those events. But there are times where people recognize me and want nothing to do with the conversation. There are times people recognize me, and that’s exactly what they want: They want to engage in an argument, or they want exposure and to be on television. More often than not, you go to these events and people want to be heard, and so that’s part of it all.

I went to [the Conservative Political Action Conference] a few years back, and I thought I would be ostracized. But I was invited in by so many people because I was part of that MAGA universe. For the people who are just there because it is a show and they’re excited to be close to the biggest story on Earth, I was a character in that story. I was one that they might want to do battle with verbally, to say the least. But I was more a curiosity than somebody to be shunned.

Have you ever had any frightening interactions?

JK: I mean, I was at an event and an insurrection broke out. Don’t always see that coming. Sometimes things get strange.

SW: You might be entitled to some money from that, I think.

JK: I’m watching the news closely. I think there’s a decent chance I get a little bit of Trump coin out of this. We’ll see what the Justice Department has to say. Otherwise, I might storm the Treasury next time I’m in town.

I’ve had a handful of very tense moments. I travel with, like, four security guards. That’s partially because I can can’t do a chin-up to save my life. I have bad feet, so my ability to flee is reduced. So I need people around me to protect me. But this is what the state of comedy is in 2026: If you want to make some political jokes out in the wild, you better come correct with a security team.

If you want to make some political jokes out in the wild, you better come correct with a security team.
Jordan Klepper

Also: I think for this upcoming show, Steve has agreed to take a bullet for me. That’s part of the contract.

SW: No, that’s the kind of whiskey I agreed to. I said I will drink a shot of Bulleit.

JK: OK, I misunderstood the agreement.

Steve, when CBS announced last summer that it was canceling “The Late Show,” what was the mood on the show?

SW: It was really kind of shocking. The whole late-night industry is changing, and so we knew that shows were trimming sails, so to speak. Seth Meyers cut his band, and Jimmy Fallon went down a few days of the week. So it wasn’t off my radar that the show might start to change or that Stephen might retire. But for CBS to just bring the ax down was not really on anybody’s bingo card, to use the overused expression.

We were all upset about it, but it never was, like, mournful or anything. I give Stephen a lot of credit for that. Our last nine months felt very celebratory.

Writing a late-night show every day is hard work. And anytime you were tempted to be like, Oh, my God, this is a hard script to write, or I don’t feel like going to work today, there was this reminder: Oh, I only get to do this a finite number of times again with these people. So I think we all had a lot of fun. I think we ended the show on our terms, and Stephen got to execute his vision for what a final show would be. So as sad as I am that it’s over, the last leg of it was really fun.

You mentioned the financial pressures, but there were obvious political motivations behind the cancellation. And the administration has targeted other performers and shows, like Jimmy Kimmel’s. What does that say about the state of entertainment and comedy?

SW: It’s interesting because, in some ways, people are consuming this content more than ever, and yet the industry is struggling to monetize it. But the fact that the administration is even paying attention to it … I mean, I think Colbert said the fact that Trump is even noticing this stuff is the saddest thing in the world. He’s got a far more important job to do. You know, Trump tweeted or Truth Socialed or whatever when we got canceled. I don’t know if he had a direct hand in it, but he wants you to think he did, which is crazy.

And then there’s his lack of sense of humor. Presidents have always been made fun of, and the fact that he’s so thin-skinned is sad.

But you’ve got a couple different things going on: You’ve got industry growing pains, and you’ve got an administration that is hostile toward being satirized. So it’s a weird time. But honestly, while I’m bummed that Stephen is not there anymore on a nightly platform, it makes me an even bigger die-hard fan of the genre, and I think a lot of people are feeling that way.

It’s far from the old days of, like, the Leno-Letterman late-night wars. It really feels like a fraternity. So I hope these shows — “The Daily Show,” “The Tonight Show,” Kimmel, John Oliver in a slightly different category, Seth — I hope they go on for as long as they can, because late night is an important tradition.

JK: I echo the good parts of what Steve said. Not all of it, but the articulate parts. ➆

This interview was edited for clarity and length.

Jordan Klepper with Steve Waltien, Friday, July 31, 7:30 p.m., at the Flynn Main Stage in Burlington. $38.71-102.20.

The original print version of this article was headlined “Funny Cuz It’s True | Comedians Jordan Klepper and Vermont native Steve Waltien talk MAGA, Colbert and comedy in the age of Trump”